4-Hydroxyphenylpyruvate dioxygenase

4-hydroxyphenylpyruvate dioxygenase
Identifiers
Symbol HPPD
Alt. symbols HPD; PPD
Entrez 3242
HUGO 5147
OMIM 609695
RefSeq NM_002150
UniProt P32754
Other data
EC number 1.13.11.27
Locus Chr. 12 q24-qter

4-Hydroxyphenylpyruvate dioxygenase HPPD is an Fe-containing enzyme, that catalyzes the second reaction in the catabolism of tyrosine - the conversion of 4-hydroxyphenylpyruvate to homogentisate.

Function

The HPPD reaction occurs through a NIH shift and involves the oxidative decarboxylation of an α-oxo acid as well as aromatic ring hydroxylation. The NIH-shift, which has been demonstrated through isotope-labeling studies, involves migration of an alkyl group to form a more stable carbocation. The shift, accounts for the observation that C3 is bonded to C4 in 4-hydroxyphenylpyruvate but to C5 in homogentisate.


See also

[2] [3] [4]

  1. ^ Fritze, I.M.; Freigang, J., Auerbach, G., Huber, R., Steinbacher, S. (2004). "The Crystal Structures of Zea mays and Arabidopsis 4-Hydroxyphenylpyruvate Dioxygenase". Plant Physiol. 134 (4): 1388–1400. doi:10.1104/pp.103.034082. PMC 419816. PMID 15084729. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=419816. ; rendered with UCSF Chimera [1]
  2. ^ Saito, I; Chujo, Y; Shimazu, H; Yamane, M; Matsuura, T; Cahnmann, Hans J. (1975). "Nonenzymic oxidation of p-hydroxyphenylpyruvic acid with singlet oxygen to homogentisic acid. A model for the action of p-hydroxyphenylpyruvate hydroxylase". Journal of the American Chemical Society 97 (18): 5272–7. doi:10.1021/ja00851a042. PMID 1165361. 
  3. ^ Wada, GH; Fellman, JH; Fujita, TS; Roth, ES (1975). "Purification and properties of avian liver p-hydroxyphenylpyruvate hydroxylase". The Journal of biological chemistry 250 (17): 6720–6. PMID 1158879. 
  4. ^ Johnson-Winters, K; Purpero, VM; Kavana, M; Nelson, T; Moran, GR (2003). "(4-Hydroxyphenyl)pyruvate dioxygenase from Streptomyces avermitilis: the basis for ordered substrate addition". Biochemistry 42 (7): 2072–80. doi:10.1021/bi026499m. PMID 12590595.